Implementations may differ, so it's best to check the man pages for your local version.
Well rather than search on Google for all the rsync and cron options on a Mac, was hoping to get some tips from users here that are already doing it and save quite a bit of time.
That's why I suggested your local man pages. From a command line, try man cron or man rsync to get the documentation for the version installed on your system.
(My systems are Linux and OpenBSD, so I'm not certain which versions Apple ships with macOS.)
Follow timstephens24 advice
Yeah it can be a little complicated since you'll have to run a find command to say for example find /path/channels -type f -mmin +120 -exec rsync etc.....
If you have Channels set to create an edl file you could look for the edl file and then if you find an edl file next to the video move the video file over...
There's a few ways to do it, but the easiest is to just leave what you have where it is and then set the DVR location to your new external and your old location as an additional storage location. Then you can copy everything over and just delete it from your old location after the copy is done and you don't have to worry about finding new items and moving it.
If you're making a new drive your primary recording storage, you should copy over the Images, Database, Logs, and Streaming folders from the old drive to the new. Those should be fairly small and quick to move.
It is not the end of the world if you don't though, because the preview images and other cache data will be regenerated.
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I think that calls for a new article 
and maybe a spell check on manageing
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Thanks for all the ideas. Its too late for me to just make the new drive the main drive, as I've moved about 3TB over already. I can use rsync to move files, which seems to work better than just manually copying it. My concern is what happens if there is a recording in flight when I do this. I'm guessing that it will copy the partial file over, but because its open that it won't be able to delete the old one and I'll end up with two copies of that file... one on the new drive that is corrupt, and one on the old drive that is good. What will Channels DVR do if this happens?
I have so many passes going that there is never a time that recording is idle unless I could manually pause it. What I've been doing when manually copying is to avoid the directories that I see have recordings going on, and keep the copy short enough to minimize the chance that a new recording will start while its running. Not exactly easy to automate so for now I"ll just go in every few weeks and manually update. Would be great if I could setup something on cron but not seeing how that would work... I know enough to be dangerous with this stuff.
Adding a secondary storage path, can i just drag and drop on my mac os desktop to the new directory the files or shows that i want to host on that other external drive?
You need to move them, not copy them... so you have to hold the function key on a Mac to make it a move. But after you do that once, then you can't really do it again because the directories for the shows will already exist.
Please add a Sports section to the additional locations. I record football games, and they are 4 hours plus. Need a special place for these monsters. Thanks.
There is only TV and Movies. Sports are a genre of TV shows. They will get filtered into a folder for the show so if the type of sporting event groups that way then you might get lucky.
(Sorry in advance for the revival)
Has anyone on Linux/MacOS tried a simple symlink to accomplish this? I would love to move some older stuff "offline" and use an SSD for the stuff i keep up with.
In my Linux container, I wanted my Data directory elsewhere and found a symlink did not work, but a bind mount did. Have not tried a bind mount within the content directory structure so unsure if it works there, but potentially worth a try.
I record to an internal SSD & then weekly use rsync to move new recordings to my second location - an external drive.
Both storage paths are in the Channels settings, no need for symlinks.
I could have the scheduled rsync happen @ any point in time - hourly, daily, weekly, etc.
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does this still work?
Does what still work?
You can add Additional Storage Locations from the DVR web UI now.
Click the + next to Storage Paths
It will then let you use a directory picker
Choose an additional storage directory for recordings
If your main DVR drive is filling up, you can move existing recording folders over to a new drive and add that as an additional storage path.
Note that new recordings will still be created on the primary DVR storage drive. Old recordings can be manually moved over, and will automatically play from the secondary drive if the video is not found on the main drive.
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You will not see additional storage as it will not use it for recording. You have to move recordings to it.
I would like to add additional drives to my raspberry pi server. Could I just put a USB hub on the pi? What else would I need to do?